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Syntheses and photophysical properties of some 4‐arylpyridinium salts
Author(s) -
Kelley Charles J.,
Ansu Kwabena,
Budisusetyo Wiranto,
Ghiorghis Alem,
Qin Yuanxi,
Kauffman Joel M.
Publication year - 2001
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570380102
Subject(s) - chemistry , intramolecular force , fluorescence , lasing threshold , aryl , alkylation , photochemistry , sulfonate , excited state , dye laser , combinatorial chemistry , organic chemistry , laser , sodium , alkyl , physics , quantum mechanics , nuclear physics , optics , catalysis
A number of 4‐arylpyridines, many methoxy substituted, were prepared by an efficient two‐step method involving aryl Grignard addition to 1‐methyl‐4‐piperidone and direct aromatization of the resulting 4‐aryl‐4‐piperidinols. The pyridines were N ‐alkylated to give sulfonate salts desired for their fluorescent properties. Study of selected compounds as laser dyes revealed several structures to be efficient dyes lasing in the 530‐550 nm range. Two new diazaquaterphenyls were prepared and were quaternized. These salts exhibited intense fluorescence in the 420‐450 nm range, but would not lase. A phenolic azaterphenyl suitably substituted for excited state intramolecular proton transfer (ESIPT) did not fluoresce at all.